CN102703019B - Liquid optical clear adhesive with low solidification energy and preparation method thereof - Google Patents
Liquid optical clear adhesive with low solidification energy and preparation method thereof Download PDFInfo
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- CN102703019B CN102703019B CN201210192485XA CN201210192485A CN102703019B CN 102703019 B CN102703019 B CN 102703019B CN 201210192485X A CN201210192485X A CN 201210192485XA CN 201210192485 A CN201210192485 A CN 201210192485A CN 102703019 B CN102703019 B CN 102703019B
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- 239000007788 liquid Substances 0.000 title claims abstract description 46
- 230000003287 optical effect Effects 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 239000000853 adhesive Substances 0.000 title abstract description 9
- 230000001070 adhesive effect Effects 0.000 title abstract description 9
- 238000007711 solidification Methods 0.000 title abstract 4
- 230000008023 solidification Effects 0.000 title abstract 4
- -1 thioalcohol compound Chemical class 0.000 claims abstract description 18
- 239000005062 Polybutadiene Substances 0.000 claims abstract description 17
- 229920002857 polybutadiene Polymers 0.000 claims abstract description 17
- 239000011347 resin Substances 0.000 claims abstract description 16
- 229920005989 resin Polymers 0.000 claims abstract description 16
- 239000004814 polyurethane Substances 0.000 claims abstract description 14
- 229920002635 polyurethane Polymers 0.000 claims abstract description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 10
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 8
- 239000004611 light stabiliser Substances 0.000 claims abstract description 5
- 108010010803 Gelatin Proteins 0.000 claims description 27
- 229920000159 gelatin Polymers 0.000 claims description 27
- 239000008273 gelatin Substances 0.000 claims description 27
- 235000019322 gelatine Nutrition 0.000 claims description 27
- 235000011852 gelatine desserts Nutrition 0.000 claims description 27
- 238000002156 mixing Methods 0.000 claims description 19
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 13
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 claims description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 claims description 9
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 7
- 239000012965 benzophenone Substances 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 claims description 5
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical group CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 claims description 5
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 5
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical group CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 4
- 239000007983 Tris buffer Substances 0.000 claims description 4
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 claims description 4
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 claims description 4
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims description 4
- 229940119545 isobornyl methacrylate Drugs 0.000 claims description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid group Chemical group C(CCCCCCCCC(=O)O)(=O)O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 4
- NQSLZEHVGKWKAY-UHFFFAOYSA-N 6-methylheptyl 2-methylprop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C(C)=C NQSLZEHVGKWKAY-UHFFFAOYSA-N 0.000 claims description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000003053 piperidines Chemical class 0.000 claims description 3
- VDVUCLWJZJHFAV-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1 VDVUCLWJZJHFAV-UHFFFAOYSA-N 0.000 claims description 2
- NOVNFHQBYJQDJA-UHFFFAOYSA-N C1(=CC=CC=C1)CC(C)=O.OCCOCCO Chemical compound C1(=CC=CC=C1)CC(C)=O.OCCOCCO NOVNFHQBYJQDJA-UHFFFAOYSA-N 0.000 claims description 2
- JXGVUKVRQBFPJH-UHFFFAOYSA-N CC1=CC(C)=C(C(=O)[P](=O)C2=CC=CC=C2)C(C)=C1 Chemical compound CC1=CC(C)=C(C(=O)[P](=O)C2=CC=CC=C2)C(C)=C1 JXGVUKVRQBFPJH-UHFFFAOYSA-N 0.000 claims description 2
- WZELXJBMMZFDDU-UHFFFAOYSA-N Imidazol-2-one Chemical class O=C1N=CC=N1 WZELXJBMMZFDDU-UHFFFAOYSA-N 0.000 claims description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 2
- UJVPXXKBKDRVTG-UHFFFAOYSA-N bis[1-(1-hydroxycyclohexa-2,4-dien-1-yl)cyclohexyl]methanone Chemical group OC1(CC=CC=C1)C1(CCCCC1)C(=O)C1(CCCCC1)C1(CC=CC=C1)O UJVPXXKBKDRVTG-UHFFFAOYSA-N 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 229910001392 phosphorus oxide Inorganic materials 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 9
- 230000008569 process Effects 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 2
- 239000003999 initiator Substances 0.000 abstract 1
- 238000001723 curing Methods 0.000 description 11
- 239000002390 adhesive tape Substances 0.000 description 7
- 238000005516 engineering process Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 230000009286 beneficial effect Effects 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 238000004383 yellowing Methods 0.000 description 2
- IMQFZQVZKBIPCQ-UHFFFAOYSA-N 2,2-bis(3-sulfanylpropanoyloxymethyl)butyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(CC)(COC(=O)CCS)COC(=O)CCS IMQFZQVZKBIPCQ-UHFFFAOYSA-N 0.000 description 1
- MBVGJZDLUQNERS-UHFFFAOYSA-N 2-(trifluoromethyl)-1h-imidazole-4,5-dicarbonitrile Chemical compound FC(F)(F)C1=NC(C#N)=C(C#N)N1 MBVGJZDLUQNERS-UHFFFAOYSA-N 0.000 description 1
- 206010023126 Jaundice Diseases 0.000 description 1
- 150000001252 acrylic acid derivatives Polymers 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
Landscapes
- Macromonomer-Based Addition Polymer (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention relates to a liquid optical clear adhesive with low solidification energy and a preparation method thereof, and belongs to the field of light-cured materials. The liquid optical clear adhesive prepared by the invention consists of the following raw materials in percentage by the gross weight of the raw materials: 14-43% of hydrogenated polybutadiene polyurethane acrylate resin, 21-56% of liquid polybutadiene resin, 14-35% of acrylate active thinner, 0.9-5% of thioalcohol compound, 1-5% of light initiator and 0.1-1% of light stabilizer, and the liquid optical clear adhesive prepared by the invention has a refractive index of 1.50-1.52 and the solidification energy which is less than 3000 mJ/cm<2>, is applicable to the abutting process of a capacitive touch screen, and is particularly applicable to an occasion with a requirement on the low solidification energy.
Description
Technical field
The present invention relates to a kind of low liquid optical lens gelatin that solidifies energy and preparation method thereof that has, belong to the photo-curing material field.
Background technology
Along with the continuous renewal of flat panel display is regenerated, touch-screen constantly is applied in the products such as mobile phone, computer as a kind of new technology, and particularly under the ordering about of mobile Internet spring tide, increasing flat panel display product adopts the capacitive touch control techniques.The capacitive touch control techniques has advantage at aspects such as multiple contact design, gesture identification, speed of response, sensitivity, wearing quality, optical characteristics than traditional electric resistance touch-control technology.According to current production technique, capacitive touch screen needs during fabrication to use a kind of adhesives each layer transparent material is assembled, and to eliminate Newton's rings and rainbow phenomena, reduces the scattering loss of light, improves the brightness and contrast of flat-panel monitor.Adhesives generally adopted OCA(optical lens gelatin Optically Clear Adhesive in the past) adhesive tape, but the liquid optical lens gelatin of LOCA() relative cost is lower, bondline thickness is controlled flexibly, is more suitable in irregular the laminating with middle large size screen.
The sealer of capacitive touch screen and conductive layer adopt glass baseplate mostly; its specific refractory power is in 1.52 left and right; so require the specific refractory power of its adhesives with it, to equate as far as possible; can reduce in a large number the refraction loss of light between interface, improve contrast gradient and the sharpness of flat-panel monitor in the high light environment.Under the severe condition such as uviolizing, hydrothermal aging, thermal shock, the optical lens gelatin need to keep the stable of the important indicators such as high transmission rate, low-yellowing simultaneously, in special process, more needs the low liquid optical lens gelatin that solidifies energy.
At present, the specific refractory power of most of liquid optical lens gelatin is lower, generally below 1.50, large with specific refractory power 1.52 differences of glass, thereby light is larger in the refraction loss at interface; In addition, the curing energy of known liquid optical lens gelatin is higher, generally at 3000mJ/cm
2Above, energy consumption is large, and production efficiency is lower.
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of low liquid optical lens gelatin that solidifies energy and preparation method thereof that has, liquid optical lens gelatin prepared by the present invention, and specific refractory power is 1.50～1.52, curing energy is less than 3000mJ/cm
2, the curing energy of existing known liquid optical lens gelatin is generally at 3000mJ/cm
2Above, the present invention compares with existing known liquid optical lens gelatin, and curing energy is lower, and therefore, the liquid optical lens gelatin of the present invention is applicable to the attaching process of capacitive touch screen, is specially adapted to low occasion of solidifying energy requirement.
The technical scheme that the present invention solves the problems of the technologies described above is as follows: a kind of liquid optical lens gelatin with low curing energy, percentage composition ratio by the raw material gross weight, by following raw material, formed, hydrogenated butadiene polymer type polyurethane acrylate resin accounts for 14～43%, the liquid polybutadiene resin accounts for 21～56%, and the esters of acrylic acid reactive thinner accounts for 14～35%, and sulfur alcohol compound accounts for 0.9～5%, light trigger accounts for 1～5%, and photostabilizer accounts for 0.1～1%.
The invention has the beneficial effects as follows: solved the high shortcoming of conventional liquid optical clear adhesive curing energy, reduced energy waste, accelerated production efficiency; And the specific refractory power of cured film is higher, specific refractory power is 1.50～1.52, has greatly reduced the refraction loss of light between screen interface, has improved contrast gradient and the sharpness of flat-panel monitor in the high light environment.
On the basis of technique scheme, the present invention can also do following improvement.
Further, described hydrogenated butadiene polymer type polyurethane acrylate resin, its structural formula is meaned by following logical formula I:
Wherein: R represents 1, hexamethylene-diisocyanate (HDI), do not comprise a kind of in the part of isocyanate groups in isophorone diisocyanate (IPDI), Methylcyclohexyl diisocyanate (HTDI), dicyclohexyl methane diisocyanate (HMDI) molecular structure; R
1Representative-C
2H
4-,-C
3H
6-,-C
4H
8-in one or more; R
2Representative-H ,-CH
3In one or both.
The beneficial effect that adopts above-mentioned further scheme is that liquid optical lens gelatin anti-yellowing property prepared by the present invention is good, and color is difficult for jaundice under the various ambient conditionss such as natural light, heat, oxygen.
Further, the molecular weight of described liquid polybutadiene resin is 500～5000, Polyoil 110(molecular weight 700～860 such as EVONIK company), Polyoil 130(molecular weight 2700～3300) in one or both mixing, its structural formula is meaned by following logical formula II:
The beneficial effect that adopts above-mentioned further scheme is that the liquid polybutadiene resin is inert fraction, reduce the double bond content of whole formula, reduced the cure shrinkage of liquid optical lens gelatin prepared by the present invention, cured glue layer shrinking percentage be little, capacity usage ratio is high, has also reduced curing energy.
Further, described esters of acrylic acid reactive thinner is one or more mixing in tetrahydrofuran (THF) acrylate, Isooctyl acrylate monomer, Isooctyl methacrylate, lauryl acrylate, lauryl methacrylate(LMA), isobornyl acrylate, isobornyl methacrylate, N,N-DMAA;
Further, described sulfur alcohol compound is one or more mixing in (TMTP) of n-dodecyl mercaptan (NDM), tertiary lauryl mercaptan (TDM), trimethylolpropane tris (3-mercaptopropionic acid ester);
Further, described light trigger is one or more mixing in alpha-alcohol ketone derivative, benzophenone and derivative thereof, acyl group phosphorous oxides;
Further, described alpha-alcohol ketone derivative is 2-hydroxyl-2 methyl-phenyl-acetone-1(light trigger 1173), 1-hydroxyl-phenylcyclohexyl ketone (light trigger 184), 2-hydroxy-2-methyl-to one or more mixing in hydroxyethyl ether phenyl-acetone (light trigger 2959);
Further, described benzophenone and derivative thereof are one or more mixing in benzophenone (BP), 4-methyldiphenyl ketone (MBP), 4,4 '-bis-(dimethylamino) benzophenone (MK);
Further, described acyl group phosphorous oxides is 2,4,6-trimethylbenzoyl-oxyethyl group-phenyl phosphorus oxide (light trigger TEPO), 2,4, one or more mixing in 6-trimethylbenzoyl-diphenyl phosphate oxidation (light trigger TPO), two (2,4,6-trimethylbenzoyl) phenyl phosphorus oxide (photoinitiator b APO);
Further, described photostabilizer is hindered amine light stabilizer;
Further, described hindered amine light stabilizer is one or more mixing in piperidine derivative, imidazolone derivatives, azacycloalkyl ketone derivatives, it is for example sebacic acid two (2,2,6,6-tetramethyl--4-hydroxy piperidine) ester (photostabilizer 770), poly-succinic (4-hydroxyl-2,2,6,6-tetramethyl--1-piperidines ethanol) ester (photostabilizer 622), two (1,2,2,6,6-pentamethyl--4-piperidyl) sebate (photostabilizer 292), 2, one or more mixing in 2,6,6-tetramethyl--4-piperidines stearate (photostabilizer 3853).
Another technical scheme that the present invention solves the problems of the technologies described above is as follows: a kind of preparation method with liquid optical lens gelatin of low curing energy, comprise: add successively hydrogenated butadiene polymer type polyurethane acrylate resin, liquid polybutadiene resin, esters of acrylic acid reactive thinner, sulfur alcohol compound, light trigger, photostabilizer in stirrer, stir, after vacuumizing and defoaming, naturally standing to room temperature, obtain.
On the basis of technique scheme, the present invention can also do following improvement.
Further, describedly draw empty vacuum tightness and be-0.1～-0.05MPa, the time is 0.1～1h.
Embodiment
Below principle of the present invention and feature are described, example, only be used to explaining the present invention, is not intended to limit scope of the present invention.
Embodiment 1
(as shown in logical formula I, R represents the part that does not comprise isocyanate groups in the hexamethylene diisocyanate molecular structure accurately to take 30g hydrogenated butadiene polymer type polyurethane acrylate; R
1Representative-C
3H
6-; R
2Representative-H), 40g liquid polybutadiene resin (Polyoil 110), 30g Isooctyl acrylate monomer, 2.5g n-dodecyl mercaptan, 4g light trigger 184,0.2g photostabilizer 770, add above-mentioned each component in stirrer successively, mix, after vacuumizing and defoaming (vacuum tightness-0.1MPa, 0.1h), naturally standing to room temperature, pack, obtain.
Embodiment 2
(as shown in logical formula I, R represents the part that does not comprise isocyanate groups in the isophorone diisocyanate molecular structure accurately to take 28g hydrogenated butadiene polymer type polyurethane acrylate; R
1Representative-C
3H
6-; R
2Representative-CH
3), 60g liquid polybutadiene resin (Polyoil 130), 15g isobornyl acrylate, 1g trimethylolpropane tris (3-mercaptopropionic acid ester), 2g photoinitiator b P, 1g light trigger TPO, 0.6g photostabilizer 622, above-mentioned each component is added in stirrer successively, mix, (vacuum tightness-0.09MPa after vacuumizing and defoaming, 0.2h), naturally standing to room temperature, pack, obtain.
Embodiment 3
Accurately take 16g hydrogenated butadiene polymer type polyurethane acrylate and (as shown in logical formula I, in R represent methylidene cyclohexyl diisocyanate molecular structure, do not comprise the part of isocyanate groups; R
1Representative-C
4H
8-; R
2Representative-CH
3), 60g liquid polybutadiene resin (Polyoil 130), 20g isobornyl methacrylate, 5g trimethylolpropane tris (3-mercaptopropionic acid ester), 4g light trigger 1173,1g light trigger TEPO, 0.2g photostabilizer 292, above-mentioned each component is added in double-planet dynamic mixing stirrer successively, mix, (vacuum tightness-0.08MPa after vacuumizing and defoaming, 0.3h), naturally standing to room temperature, pack, obtain.
Embodiment 4
(as shown in logical formula I, R represents the part that does not comprise isocyanate groups in the dicyclohexyl methane diisocyanate molecular structure accurately to take 43g hydrogenated butadiene polymer type polyurethane acrylate; Left end R
1Representative-C
2H
4-C
3H
6-, right-hand member R
1Representative-C
4H
8-; R
2Representative-CH
3), 22g liquid polybutadiene resin (Polyoil 110), 18g lauryl methacrylate(LMA), the 12g isobornyl acrylate, the tertiary lauryl mercaptan of 2g, 3g light trigger MK, 0.3g photoinitiator b APO, 0.1g photostabilizer 3853, add above-mentioned each component in double-planet dynamic mixing stirrer successively, mix, after vacuumizing and defoaming (vacuum tightness-0.07MPa, 0.5h), naturally standing to room temperature, pack, obtain.
Embodiment 5
Accurately take 33g hydrogenated butadiene polymer type polyurethane acrylate and (as shown in logical formula I, in R represent methylidene cyclohexyl diisocyanate molecular structure, do not comprise the part of isocyanate groups; Left end R
1Representative-C
2H
4-C
3H
6-C
4H
8-, right-hand member R
1Representative-C
2H
4-C
4H
8-; R
2Representative-CH
3), 45g liquid polybutadiene resin (Polyoil 130), 8g tetrahydrofuran (THF) acrylate, the 12g lauryl methacrylate(LMA), 3g n-dodecyl mercaptan, 1g light trigger 184,0.3g photoinitiator b APO, 0.05g photostabilizer 3853, add above-mentioned each component in stirrer successively, mix, after vacuumizing and defoaming (vacuum tightness-0.06MPa, 0.7h), naturally standing to room temperature, pack, obtain.
Embodiment 6
(as shown in logical formula I, R represents the part that does not comprise isocyanate groups in the dicyclohexyl methane diisocyanate molecular structure accurately to take 17g hydrogenated butadiene polymer type polyurethane acrylate; Left end R
1Representative-C
2H
4-, right-hand member R
1Representative-C
3H
6-; Left end R
2Representative-H, right-hand member R
2Representative-CH
3), 50g liquid polybutadiene resin (Polyoil 110), 28g Isooctyl methacrylate, the 12g isobornyl methacrylate, the tertiary lauryl mercaptan of 4g, 3g light trigger 2959,0.3g photoinitiator b APO, 0.1g photostabilizer 770, add above-mentioned each component in stirrer successively, mix, after vacuumizing and defoaming (vacuum tightness-0.05MPa, 1h), naturally standing to room temperature, pack, obtain.
Experimental example 1
By the following method the sample of embodiment 1～6 and existing known optical transparent adhesive tape 1 and 2 have been carried out to the contrast test of curing energy and specific refractory power, test result is as shown in table 1.
Known optical transparent adhesive tape 1: accurately take 20g polybutadiene-modified acrylate TE2000 (Japanese Cao Da Chemical Co., Ltd), 40g liquid polybutadiene resin (Polyoil 110), 28g Isooctyl acrylate monomer, 3g light trigger 184,0.5g light trigger TPO, above-mentioned each component is added in stirrer successively, mix, (vacuum tightness-0.09MPa after vacuumizing and defoaming, 1h), naturally standing to room temperature, pack, obtain.
Known optical transparent adhesive tape 2: accurately take the two key chemical incs in 30g aliphatic urethane acrylate 5191(Taiwan), the 30g Isooctyl acrylate monomer, 3g light trigger 184,0.5g light trigger TPO, add above-mentioned each component in stirrer successively, mix, after vacuumizing and defoaming (vacuum tightness-0.09MPa, 1h), naturally standing to room temperature, pack, obtain.
Solidify the energy test method: dsc (UV-DSC), the DSC-Q2000 of U.S. TA company, 25 ℃, UV light intensity 30mW/cm
2.
Refraction index test: Abbe refractometer.
The sample that table 1 embodiment 1-6 makes and known optical transparent adhesive tape performance comparison test result
| Sample | Specific refractory power | Solidify energy mJ/cm 2 |
| The sample of embodiment 1 | 1.512 | 1469 |
| The sample of embodiment 2 | 1.511 | 1508 |
| The sample of embodiment 3 | 1.512 | 1516 |
| The sample of embodiment 4 | 1.512 | 1472 |
| The sample of embodiment 5 | 1.511 | 1459 |
| The sample of embodiment 6 | 1.512 | 1530 |
| Known optical transparent adhesive tape 1 | 1.482 | 2789 |
| Known optical transparent adhesive tape 2 | 1.476 | 3016 |
From the above results, can find out, compared with the prior art, specific refractory power is higher, has lower curing energy, can reduce energy waste, greatly faster production efficiency for the liquid optical lens gelatin of the present invention.
The foregoing is only preferred embodiment of the present invention, in order to limit the present invention, within the spirit and principles in the present invention not all, any modification of doing, be equal to replacement, improvement etc., within all should being included in protection scope of the present invention.
Claims (7)
1. one kind has the low liquid optical lens gelatin that solidifies energy, it is characterized in that, described liquid optical lens gelatin is by the percentage composition ratio of raw material gross weight, following raw material, consist of, hydrogenated butadiene polymer type polyurethane acrylate resin accounts for 14～43%, and the liquid polybutadiene resin accounts for 21～56%, the esters of acrylic acid reactive thinner accounts for 14～35%, sulfur alcohol compound accounts for 0.9～5%, and light trigger accounts for 1～5%, and photostabilizer accounts for 0.1～1%.
2. liquid optical lens gelatin according to claim 1, is characterized in that, the structural formula of described hydrogenated butadiene polymer type polyurethane acrylate resin means with following logical formula I:
Wherein: R represents a kind of in the part that does not comprise isocyanate groups in hexamethylene diisocyanate, isophorone diisocyanate, Methylcyclohexyl diisocyanate, dicyclohexyl methane diisocyanate molecular structure; R
1Representative-C
2H
4-,-C
3H
6-,-C
4H
8-in one or more; R
2Representative-H ,-CH
3In one or both;
The molecular weight of described liquid polybutadiene resin is 500～5000, and its structural formula is meaned by following logical formula II:
3. according to the arbitrary described liquid optical lens gelatin of claim 1 or 2, it is characterized in that, described esters of acrylic acid reactive thinner is one or more mixing in tetrahydrofuran (THF) acrylate, Isooctyl acrylate monomer, Isooctyl methacrylate, lauryl acrylate, lauryl methacrylate(LMA), isobornyl acrylate, isobornyl methacrylate; Described sulfur alcohol compound is one or more mixing in n-dodecyl mercaptan, tertiary lauryl mercaptan, trimethylolpropane tris (3-mercaptopropionic acid ester); Described light trigger is one or more mixing in alpha-alcohol ketone derivative, benzophenone and derivative thereof, acyl group phosphorous oxides; Described photostabilizer is hindered amine light stabilizer.
4. liquid optical lens gelatin according to claim 3, is characterized in that, described alpha-alcohol ketone derivative is 1-hydroxyl-phenylcyclohexyl ketone, 2-hydroxy-2-methyl-to one or more mixing in hydroxyethyl ether phenyl-acetone; Described benzophenone and derivative thereof are one or more mixing in benzophenone, 4-methyldiphenyl ketone, 4,4 '-bis-(dimethylamino) benzophenone; Described acyl group phosphorous oxides is 2,4,6-trimethylbenzoyl-oxyethyl group-phenyl phosphorus oxide, 2,4, one or more mixing in 6-trimethylbenzoyl-diphenyl phosphate oxidation, two (2,4,6-trimethylbenzoyl) phenyl phosphorus oxide; Described hindered amine light stabilizer is one or more mixing in piperidine derivative, imidazolone derivatives, azacycloalkyl ketone derivatives.
5. liquid optical lens gelatin according to claim 4, is characterized in that, described piperidine derivative is sebacic acid two (2,2,6,6-tetramethyl--4-hydroxy piperidine) ester, poly-succinic (4-hydroxyl-2,2,6,6-tetramethyl--1-piperidines ethanol) ester, two (1,2,2,6,6-pentamethyl--4-piperidyl) sebate, 2, one or more mixing in 2,6,6-tetramethyl--4-piperidines stearate.
6. one kind has low preparation method of solidifying the liquid optical lens gelatin of energy, it is characterized in that, comprise: add successively hydrogenated butadiene polymer type polyurethane acrylate resin, liquid polybutadiene resin, esters of acrylic acid reactive thinner, sulfur alcohol compound, light trigger, photostabilizer in stirrer, stir, after vacuumizing and defoaming, naturally standing to room temperature, obtain
Wherein, described liquid optical lens gelatin is by the percentage composition ratio of raw material gross weight, by following raw material, formed, hydrogenated butadiene polymer type polyurethane acrylate resin accounts for 14～43%, the liquid polybutadiene resin accounts for 21～56%, and the esters of acrylic acid reactive thinner accounts for 14～35%, and sulfur alcohol compound accounts for 0.9～5%, light trigger accounts for 1～5%, and photostabilizer accounts for 0.1～1%.
7. the preparation method of liquid optical lens gelatin according to claim 6, is characterized in that, the described vacuum tightness vacuumized is-0.1～-0.05MPa, the time is 0.1～1h.
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| JP6414479B2 (en) * | 2014-02-06 | 2018-10-31 | 荒川化学工業株式会社 | UV curable adhesive composition for optics, the cured layer and optical member |
| CN103980821B (en) * | 2014-05-16 | 2015-12-09 | 烟台德邦科技有限公司 | A kind of Liquid optical clear adhesive and preparation method thereof |
| EP3184568A1 (en) * | 2015-12-21 | 2017-06-28 | Evonik Degussa GmbH | Acrylate-terminated urethane polybutadienes from low-monomer 1:1 monoadductes from reactive olefinic compounds and diisocyanates and hydroxy-terminated polybutadienes for liquid optically clear adhesives (locas) |
| JP6697306B2 (en) * | 2016-03-31 | 2020-05-20 | ハリマ化成株式会社 | Photocurable composition with moisture curing, conformal coating agent and cured product |
| CN107903829A (en) * | 2017-10-31 | 2018-04-13 | 芜湖辉灿电子科技有限公司 | A kind of transparent OCA optical cements of mobile phone screen |
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| JP2005272773A (en) * | 2004-03-26 | 2005-10-06 | Toagosei Co Ltd | Active energy beam-curable composition for optical material |
| CN101560370A (en) * | 2009-05-15 | 2009-10-21 | 烟台德邦科技有限公司 | Light-curable adhesive with shock absorption property |
| CN102010494B (en) * | 2010-09-30 | 2012-06-27 | 烟台德邦电子材料有限公司 | Light-cured resin with low water absorption and preparation method thereof |
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